Synthesis and characterization of 4′-amino and 4′-nitro derivatives of 4-N,N-dimethylaminotriphenylmethane as precursors for a proximate malachite green metabolite

被引：12

作者：

Cho, BP ^{[1
]}

Blankenship, LR ^{[1
]}

Moody, JD ^{[1
]}

Doerge, DR ^{[1
]}

Beland, FA ^{[1
]}

Culp, SJ ^{[1
]}

机构：

[1] Natl Ctr Toxicol Res, Jefferson, AR 72079 USA

来源：

TETRAHEDRON | 2000年 / 56卷 / 38期

关键词：

malachite green; nitration; nitro-dediazoniation; hydro-dediazonation; nitrosamines;

D O I：

10.1016/S0040-4020(00)00649-9

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

This paper describes the preparation of 4'-amino (2) and 4'-nitro (3) derivatives of 4-N,N-dimethylaminotriphenylmethane as precursors for presumed DNA-binding metabolites of malachite green. The primary amine 2 was synthesized via a condensation of 4-lithiated bis-(N,N-trimethylsilyl)aniline and 4-(dimethylamino)benzophenone. A simple nitro-dediazoniation reaction of 2 failed to afford 3, but gave exclusively a mixture derived from hydro-dediazoniation followed by nitration and N-dealkylative-N-nitrosation. Direct nitration of N,N-dimethylaminotriphenylmethane, however, afforded 3 as well as other nitro isomers. Published by Elsevier Science Ltd.

引用

页码：7379 / 7388

页数：10

共 30 条

[1] POSTCOLUMN REACTION FOR SIMULTANEOUS ANALYSIS OF CHROMATIC AND LEUCO FORMS OF MALACHITE GREEN AND CRYSTAL VIOLET BY HIGH-PERFORMANCE LIQUID-CHROMATOGRAPHY WITH PHOTOMETRIC DETECTION [J].